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Conklin was one of three children who grew up in a violent household. When he was eight, his mother was found burned to death in the family garden. Although first judged a suicide, his father, a devoutly religious man who hoped his son would be a minister, was eventually charged with murder, but found not guilty at trial.

Conklin won first prize when he gave a recitation at a community festival. A few years later, he ran away from home after vowing to a friend he would never return, a promise he kept. Heading to Des Moines he found employment as a hotel bellhop, but then moved to Omaha, Nebraska where his interest in theatre led to a career in comedic acting. In St. Louis, Missouri, he saw a performance by the vaudeville team of Joe Weber and Lew Fields, which prompted Conklin to develop a character based on his boss at the time, a man with a thick accent and a bushy walrus moustache. With this character, Conklin broke into vaudeville, and spent several years touring with various stock companies, doing vaudeville shows, minstrel shows, as well as clown work with a travelling circus.

After seeing several Mack Sennett comedies while in Venice, California during the 1913 winter break, the 27-year-old Conklin went to Keystone Studios, applied for a job and was hired as a Keystone Kop with a salary of $3 a day. Sennett directed him in his first film, a comedy short titled Hubby's Job.[1]

While at Keystone, Conklin became most famous when he was teamed up with the robust comic Mack Swain to make a series of comedies. With Swain as "Ambrose" and Conklin as the grand mustachioed "Walrus", they performed these roles in several films including The Battle of Ambrose and Walrus and Love, Speed and Thrills, both made in 1915. Beyond these "Ambrose & Walrus" comedies, the two appeared together in twenty-six different films.

Conklin's career hit bottom in the 1950s, and he took work as a department-store Santa Claus to make ends meet.[2] In the 1960s, Conklin was living at the Motion Picture Country Home and Hospital when he fell in love with another patient there, June Gunther. The two got married in Las Vegas in 1965, his fourth marriage and her fourth,[4] and set up housekeeping in Van Nuys, California; the groom was seventy-nine and the bride sixty-five.[2] Conklin made one last film after that, a Western comedy, A Big Hand for the Little Lady, released in 1966.

Chester Conklin died in Autumn 1971 in California at the age of 85.[5] He was cremated and his ashes were given to his family. Following his death, his great nephew, Robert Stoltz, along with his sisters rested his ashes at sea in the Pacific Ocean.

For his contribution to the motion picture industry, Conklin has a star on the Hollywood Walk of Fame at 1560 Vine Street.[6]